(Trifluoromethyl)benzene → HCID 86701272, compound
Reaction equation
[O-]S(C(F)(F)F)(=O)=O.C(OC1C=CC=C[N+]=1C)C1C=CC=CC=1.F[C:25](F)(F)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:34]([O:39][C@@H:40]1[C@@H:48]([CH2:49][CH2:50][OH:51])[C:47](=[O:52])[O:46][CH2:45][C@H:44]([NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[C:43](=[O:61])[O:42][C@H:41]1[CH3:62])(=[O:38])[CH:35]([CH3:37])[CH3:36]>>[C:34]([O:39][C@@H:40]1[C@@H:48]([CH2:49][CH2:50][O:51][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:47](=[O:52])[O:46][CH2:45][C@H:44]([NH:53][C:54]([O:56][C:57]([CH3:58])([CH3:60])[CH3:59])=[O:55])[C:43](=[O:61])[O:42][C@H:41]1[CH3:62])(=[O:38])[CH:35]([CH3:37])[CH3:36]Participants
Conditions
- Temperature
- 83 °C
Procedure
A mixture of 2-benzyloxy-1-methylpyridinium triflate (255 mg, 0.73 mmol), α,α,α-trifluorotoluene (PhCF3, 0.75 mL), MgO (30 mg, 0.74 mmol), and (3S,6S,7R,8R)-3-(tert-butoxycarbonylamino)-8-(2-hydroxyethyl)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (150 mg, 0.36 mmol) was heated at 83° C. for 1 day (d). The reaction mixture was cooled to room temperature (about 22° C.) and filtered through Celite®. The filtrate was concentrated under vacuum and purified by column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (66 mg, 36%): 1H NMR (300 MHz, CDCl3) δ 7.40-7.21 (m, 5H), 5.28 (m, 2H), 5.06 (t, J=10.0 Hz, 1H), 4.95-4.73 (m, 2H), 4.69 (s, 2H), 4.42 (s, 2H), 3.52-3.33 (m, 3H), 2.77 (td, J=11.5, 2.8 Hz, 1H), 2.60 (dq, J=14.0, 7.0 Hz, 1H), 1.42 (s, 9H), 1.26 (d, J=6.2 Hz, 3H), 1.19 (dd, J=7.0, 2.5 Hz, 6H); ESIMS m/z 530 ([M+Na]+).
Workup
- temperatureThe reaction mixture was cooled to room temperature (about 22° C.)
- filtrationfiltered through Celite®
- concentrationThe filtrate was concentrated under vacuum
- custompurified by column chromatography (SiO2, hexanes/EtOAc gradient)
Sources & evidence
- ORD record
- ord-c63d7d4bd96e438e859716a82c4f732d
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09131690B2
Reaction notes
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